(R)-5-(5,5-Dimethyl-2-oxo-2λ⁵-[1,3,2]dioxaphosphinan-2-yl)-2,6-dimethyl-4-(3-nitro-phenyl)-1,4-dihydro-pyridine-3-carboxylic acid 2,2-dimethyl-propionyloxymethyl ester

Base Information

• Chemical Name: (R)-5-(5,5-Dimethyl-2-oxo-2λ⁵-[1,3,2]dioxaphosphinan-2-yl)-2,6-dimethyl-4-(3-nitro-phenyl)-1,4-dihydro-pyridine-3-carboxylic acid 2,2-dimethyl-propionyloxymethyl ester
• CAS No.: 170308-21-1
• Molecular Formula: C₂₅H₃₃N₂O₉P
• Molecular Weight: 536.519
• Mol file: 170308-21-1.mol

Synonyms:(R)-5-(5,5-Dimethyl-2-oxo-2λ⁵-[1,3,2]dioxaphosphinan-2-yl)-2,6-dimethyl-4-(3-nitro-phenyl)-1,4-dihydro-pyridine-3-carboxylic acid 2,2-dimethyl-propionyloxymethyl ester

Chemical Property of (R)-5-(5,5-Dimethyl-2-oxo-2λ⁵-[1,3,2]dioxaphosphinan-2-yl)-2,6-dimethyl-4-(3-nitro-phenyl)-1,4-dihydro-pyridine-3-carboxylic acid 2,2-dimethyl-propionyloxymethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-5-(5,5-Dimethyl-2-oxo-2λ⁵-[1,3,2]dioxaphosphinan-2-yl)-2,6-dimethyl-4-(3-nitro-phenyl)-1,4-dihydro-pyridine-3-carboxylic acid 2,2-dimethyl-propionyloxymethyl ester

There total 2 articles about (R)-5-(5,5-Dimethyl-2-oxo-2λ⁵-[1,3,2]dioxaphosphinan-2-yl)-2,6-dimethyl-4-(3-nitro-phenyl)-1,4-dihydro-pyridine-3-carboxylic acid 2,2-dimethyl-propionyloxymethyl ester which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 52.0%

2-methoxy-5,5-dimethyl-1,3,2-dioxaphosphorinane (1005-69-2) + (R)-5-Bromo-2,6-dimethyl-4-(3-nitro-phenyl)-1,4-dihydro-pyridine-3-carboxylic acid 2,2-dimethyl-propionyloxymethyl ester (178484-40-7) → (R)-5-(5,5-Dimethyl-2-oxo-2λ5-[1,3,2]dioxaphosphinan-2-yl)-2,6-dimethyl-4-(3-nitro-phenyl)-1,4-dihydro-pyridine-3-carboxylic acid 2,2-dimethyl-propionyloxymethyl ester (170308-21-1)

Guidance literature:

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; triethylamine; In toluene; at 110 ℃; for 5h;

DOI:10.1248/cpb.44.1132

Reference yield:

(S)-(+)-1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)-5-pivaloyloxymethoxycarbonyl-3-pyridinecarboxylic acid (138279-20-6) → (R)-5-(5,5-Dimethyl-2-oxo-2λ5-[1,3,2]dioxaphosphinan-2-yl)-2,6-dimethyl-4-(3-nitro-phenyl)-1,4-dihydro-pyridine-3-carboxylic acid 2,2-dimethyl-propionyloxymethyl ester (170308-21-1)

Guidance literature:

Multi-step reaction with 2 steps

1: pyridinium bromide perbromide / CH₂Cl₂ / -20 °C

2: 52 percent / Pd(PPh₃)4, NEt₃ / toluene / 5 h / 110 °C

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; pyridinium hydrobromide perbromide; triethylamine; In dichloromethane; toluene;

DOI:10.1248/cpb.44.1132

Reference yield: 43.0%

(R)-5-(5,5-Dimethyl-2-oxo-2λ5-[1,3,2]dioxaphosphinan-2-yl)-2,6-dimethyl-4-(3-nitro-phenyl)-1,4-dihydro-pyridine-3-carboxylic acid 2,2-dimethyl-propionyloxymethyl ester (170308-21-1) → (R)-5-(5,5-Dimethyl-2-oxo-2λ5-[1,3,2]dioxaphosphinan-2-yl)-2,6-dimethyl-4-(3-nitro-phenyl)-1,4-dihydro-pyridine-3-carboxylic acid (111495-28-4)

Guidance literature:

With sodium hydroxide; In methanol;

DOI:10.1248/cpb.44.1132

upstream raw materials:

2-methoxy-5,5-dimethyl-1,3,2-dioxaphosphorinane

(R)-5-Bromo-2,6-dimethyl-4-(3-nitro-phenyl)-1,4-dihydro-pyridine-3-carboxylic acid 2,2-dimethyl-propionyloxymethyl ester

(S)-(+)-1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)-5-pivaloyloxymethoxycarbonyl-3-pyridinecarboxylic acid

Downstream raw materials:

(R)-5-(5,5-Dimethyl-2-oxo-2λ⁵-[1,3,2]dioxaphosphinan-2-yl)-2,6-dimethyl-4-(3-nitro-phenyl)-1,4-dihydro-pyridine-3-carboxylic acid